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Hydrochloric Acid → 3-Fluoro-4-[6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]quinolin-4-oxy]aniline

HRID 68536
Notes
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Reaction equation

HRID 68536 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[O:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][CH:14]=1>[Fe].CCO>[F:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][CH:14]=1)[NH2:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866969174-(2-Fluoro-4-nitrophenyloxy)-6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]quinoline

Product 1

HCID 866969183-Fluoro-4-[6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]quinolin-4-oxy]anilineYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (61.42 g, 1.1 mol) and hydrochloric acid (6 mL) were added to 90% EtOH (25v/w, 1210 mL). The mixture was warmed up to 80° C. and stirred for 15 min. Then Intermediate VIII (48.42 g, 0.11 mol) was added in batch to the reaction solution. After the addition completion, the reaction was conducted under reflux for 2 h. After completion of the reaction, the reaction was filtered by suction when it is still hot. The filtrate was collected. The solvate was evaporated off to produce a yellow solid (43 g) in a yield of 95%.

Workup

  1. temperatureunder reflux for 2 h
  2. customAfter completion of the reaction
  3. filtrationthe reaction was filtered by suction when it
  4. customThe filtrate was collected
  5. customThe solvate was evaporated off

Sources & evidence

ORD record
ord-790b59523fa345bbac27cb895099891d
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822465B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes